Ash's Lustful Desires
by D-nasty
Summary: After fulfilling his dream and having a successful career, Ash finds himself lonely and seeks a woman's touch. What started out as one woman he starts having multiple woman come into his life filling the void. Watch as Ash gets to sleep with multiple women and loving them. A pure smut pokemon story.


**Well it's my birthday again and I have a new story. Hope you love it.**

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Chapter 1 Jumping Jessie

We come to a large mansion in Kanto surrounded by the forest where we see a 24 year old Ash Ketchum sitting in his living room watching tv relaxing wearing a blue muscle shirt and black shorts. He's changed alot over the years, he now stood six feet tall was lean and musculare like a swimmers body having tight muscles all over him sporting a six-pack cause of all the training he's done, he hair was still messy but had gotten longer to where it reached his shoulders and his brown eyes had a tint of blue in them showing power and wisdom from the aura training he went under.

After he became a Pokemon Master Ash decided to take Scoff on his offer and become a Frontier Brain with it he had more money than ever which increased his already large bank account since becoming a Pokemon Master, got to expand his battle senses, and become a famous even more famous trainer.

But even though he had a successful life, Ash found himself getting a little lonely wanting a female companion to greet him and love him when he came home after traveling a little while. That got Ash thinking of all the women he encountered and know throughout all his life, and wondered what life would be like if they were here right now.

He was thrown out of his thoughts when he heard a shout coming from outside. Decided to see what was going on Ash put on some shoes and went outside into the forest following the sounds of shouting. When he came into a clearing he saw a woman being surrounded by six men that had three Rhydon and three Ursaring.

"Leave me alone, you brutes!" The woman shouted.

"Don't be like that sweety." One of the men said.

"Yeah, we already beat your Pokemon, so why don't you just give in." Another one laughed.

"We'll promised you'll like it." Another one chuckled his voice dripping in lust.

"I would rather die then get with you!" The woman shouted.

"That can be arranged after we're through with you." Another one of the men snickered as did the other men and they advanced on the woman who backed up in fear while the Pokemon made sure she didn't have anywhere to escape from.

Knowing what these scumbags were going to do made Ash growl in anger and digust as he unclipped a pokeball and unleashed one of his Pokemon which happend to be Charizard.

"Charizard, use Steel Wing!" Ash commanded.

Charizard roared getting everyone's attention as his wings glowed white and he flew into the two Rhydon and one Ursaring knocking them to the ground unconcious.

"What the?!"

"Who's this fucker?!"

"Rhydon, use Rock Blast!"

"Ursaring, use Hyper Beam!"

Rhydon launched a barrage of rocks while the two Ursaring fired orange beams of energy from their mouths.

"Charizard, meet that their attacks with Overheat!" Ash said swiping his left arm away.

Charizard reared his head back and fired a large firey blast from his mouth meeting his foes attack, they struggled for a minute before Charizard's attack overpower theirs and nailed the Pokemon knocking them to the ground knocked out.

"No way!"

"That Charizard beat our Pokemon in one move!"

"Grab the bitch! If we use her as hostage maybe we can win."

"I don't think so!" Ash said jumping over Charizard returning him and landed in front of the woman getting in a fighting position. "You want her, you have to go through me."

"Gladly." The men shouted as they charged at Ash thinking it if they fought together they could win.

However one beatdown later they were all knocked out on the ground twitching and moaning with pain while Ash didn't have a scratch on him and wasn't even winded.

"Asshole." Ash spat before turning to the woman. "You alright miss?"

"Yes, thank you." The woman thanked looking to her savior.

However when they saw each other they got one hell of a surprise.

"Jessie?!"

"The twerp?!"

Ash and the now revealed Jessie was looking at each other in shock. It's been years since they last saw each other after another failed attempt to catching his Pikachu. For Ash he was seeing that the years have been good to his old foe, she looked for beautiful that when he was a kid as she looked like she has been taking good care of herself, her stomach seemed have to gotten tighter and her breasts looked bigger now sporting a E-cup. For Jessie she saw that the twerp had really filled out, he looked taller, more muscular, and dare she even say more handsomer than those male supermodels you see in the magazine or news.

Realizing that they were both checking each other out Ash and Jessie looked away from one another a little flushed.

"So, um, what are you doing out here, Jessie?" Ash asked.

"I was trying to find a hotel to sleep in when those bastard cornered me, beat my Pokemon, and were looking to get lucky." Jessie frowned.

"Good thing I came out here when I heard shouting." Ash said.

"You camping here or something?" Jessie asked.

"Oh no, I live here. In a mansion that's a few feet away." Ash said thumbing backwards.

"Heh, guess you really moved up in the world, huh twerp?" Jessie smirked.

"You could say that." Ash chuckled before looking at her. "If you want you can stay over at my place if you have nowhere to go."

"Why would you help me? After everything we've been through?" Jessie wondered.

"It's all in the past with me. Beside helping you is he right thing to do." Ash said.

Jessie looked at his eyes to see any deceit only to find none. She chuckling shaking her head.

"Even after all this time your still that kind-hearted twerp." She said.

"Hey, does this look like the body of a twerp?" Ash grinned flexing his muscles.

"Got me there." Jessie laughed.

After calling Officer Jenny to arrest the men and have their Pokemon taken away Ash and Jessie made their way to Ash's mansion.

"Damn twerp! Your house is big!" Jessie exclaimed.

"One of the perks of being a Frontier Brain." Ash laughed.

They went into the mansion and Ash gave Jessie the grand tour of the place and she was impressed with what she saw. After a few minutes Ash was back in the living room watching tv while Jessie decided to take a shower to ease her worries of the experience that was about to happen to her.

"Looks like Dawn's doing good for herself." Ash smiled watching how Dawn won another contest in her dress with Togekiss behind her as she waved to the crowd. "And she's really filled out." He mutters eyeing her CC-cupe breasts in her dress.

"Thinking pervy thoughts about your friend on tv?" Jessie's teasing voice said behind him.

"Hey I'm a healthy lusting grown man. I can think those kinds of thoughts about my friends if I want to." Ash retorted turning to Jessie but upon seeing her he got a nosebleed and he felt himself getting hard.

Jessie was wearing a blue tube top and black short shorts but some of her was still dripping wet body and her hair was out of her usual style and flowing down to her tight ass. All and all she was literly a wet dream. Jessie seeing his look smirked seductively.

"Like what you see?" She purred at Ash.

"What's not to like about seeing a sexy woman such as yourself." He said smoothly shrugging his shoulders and looked away wiping his nose hiding his smirk when he heard Jessie sputter in surprise and embarassment.

"Well I see you've definately changed over the years." Jessie commented sitting down beside him.

"Yeah. So are you still with Team Rocket?" Ash asked.

"Believe it or not, I quited after the boss kept saying how much of a failure I was and that I'll never amount to anything." Jessie sighed bringing her legs to her chest and wrapped her arms around them.

"So what have you been doing?" Ash wondered.

"I've been traveling around, taking odd jobs to support myself, and training my Pokemon whenever I can. But seeing as how they were beaten tonight I didn't train them good enough. I guess I never will amount up to anything." Jessie muttered.

"That's not true." Ash said scooting closer to her. "For all the years you've spent trying to capture my Pikachu or other Pokemon you've shown determination, careful planing, and a will to never give up even when things don't go your way. And if your boss can't see those as good qualities, then he's a idiot."

Jessie was surprised of what Ash said about her, and it flet nice to have someone say something nice about her.

"Thanks, your very sweet for that twer- I mean Ash." Jessie smiled at him.

"I think that's the first time you said my name." Ash chuckled.

"Yeah, well I've changed." Jessie giggled brushing her shoulder against his.

Ash smirked before pushing her back. Jessie took this as a challenge and pounced on Ash where they began to wrestle laughing their heads off. After the tussle Ash had Jessie pin down holding her wrists.

"Whoa! When did you get so strong?" Jessie asked surprised.

"Same time the boys got lower." Ash smirked.

Jessie laughed before she saw their position and blushed. Ash saw this and thought she looked cute. And seeing her like this and how she turned out over the years made Ash act on impulse bringing his face down towards hers and kissed her right on the lips shocking her.

 _"Ash, is kissing me! My first kiss!"_ Jessie screamed in her mind. What many didn't know is that Jessie had bad luck with men only being attracted to her body or using her for their own sick amusement, she tried to find love but she was always hurt by those who pretended to care for her. After getting over the shock and feeling his lips on hers she started to ease into the kiss kissing Ash back with much vigor.

Ash's hand let go of Jessie's wrists and trailed down her body to before they reached her ass and he groped her cheeks making her moan in pleasure. Jessie's hands went under his shirt feeling his hard muscles making her shiver in anticipation. They seperated and looked deep into each others eyes and saw lust for one another.

"Jessie, if you're up for this, I'll continue." Ash whispered.

"I want this Ash. I want you." Jessie whispered back.

Both sat up as Ash took his shirt off showing his tight phisyic and Jessie took hers off too showing her tits as she wasn't wearing a bra.

"Nice body." Ash smiled.

"You too." Jessie smiled.

Ash took Jessie's shorts off showing her pussy were gushing having a triangle trimmed patch of hair above her lips. Jessie then decided to take Ash's shorts along with his boxers off and got a shocking surprise seeing his hard dick.

 _"Oh my Arceus! He's got to be 13 inches long! How does he hide a monster like that?!"_ Jessie thought with wide eyes.

"Don't tell me you're intimidated." Ash smirked.

"I'll show you intimidated." Jessie chastised Ash taking a hold of his tool in her hand laying down with her bust resting on the top part of his legs. "When I'm through with you, you'll be begging me to cum." She promised with a smirk.

Ash was groaning hard as Jessie was slowly jerking him off with her tongue licking his somewhat leaking head. It showed that she wasn't experienced in this as the grip was a little tight, but not uncomfortable.

Swirling her tongue around the head, Jessie moaned when she tasted his pre-cum. Liking the taste and wanting more, she took her hand off his member and took him deeper, now taking nine inches of his prick in her throat. _"So big!"_ Jessie gagged as she had tears welling in her eyes. She could feel her throat stretching around the massive meat. It made her core hot.

"Damn Jessie! That feels good!" Ash groaned, gripping the couch hard with his legs shaking a little. Her tongue licked and slurped his lower head as she slowly bobbed up and down. Ash moaned in delight feeling the vibrations of Jessie's soft gurgle.

 _"This is making me so hot! I want to taste more!"_ Jessie thought blushing hard. She went deeper down his dick extending her throat stuffing the last 4 inches making her pussy gush more of her juices. _"All of his cock in inside my throat."_ Jessie moaned diliriously bobbing her head on his cock more letting one of her left hand fondle his tightening junk and her other hand run down her body reaching her pussy where she began to stroke it furiously making in burn with pleasure.

"Jessie, if you keep that up, I'll cum!" Ash warned his bobbing lover who answered by speeding up her thrusts and sucking on his tool more. "S-Shit!" Spit flew from his mouth as Ash threw his head back. It was hard to not grab her head and skull-fuck her but, he stayed letting her go at her own pace.

"I'm just getting started." Jessie said taking her mouth off his manhood and her hands off his balls or out of her twat and squashed her lovely mammaries around his hot rod. "Ah! It feels so hot around my boobs." She moaned hotly as she jerked him off with her melons.

"So... fucking soft!" Ash's eyes rolled in the back of his head. A stupid smile graced his lips as he was getting a wondrous titty-fuck. "Arcues Jessie! I'm gonna cum! Gonna cum inside your mouth!" He roared as she reintroduced her mouth to his cock head.

Jessie smiled around his tip as she felt more and more juices spurt into her waiting throat. The beauty was craving his actual semen instead of his pre-jizz. _"Cum already, Ash! Cum inside my throat!"_ She thought in lust as she shook her bottom in the air, trying to cool off her steaming hot pussy.

Feeling her mouth, her soft tits along his cock, and her jiggling ass in the air was too much stimulation for the Frontier Brain. "FUCK!" Thrusting his tower all the way to her mouth was all the warning Jessie got as Ash shot his load deep into her amazingly tight throat.

Jessie's eyes flew wide open as the already thick shaft stretching her throat expanded further, causing her to gag as Ash started hosing her throat down with his thick cum. Being unprepared, some of the cum shot out her nose and poured back out her mouth coating Ash's dick before dripping down to coat her large jugs, sliding into her impressive cleavage before she got her bearings and started swallowing the near cup-sized blasts of jizz. The taste of it made her cum violenty spraying her juices all over the couch. For nearly two minutes she was forced to gulp down the thick creamy liquid before Ash stopped thrusting. Jessie slowly slid his softing erection out her mouth, gently sucking the entire way till she released him from her mouth with a loud pop. Not done cumming yet, Ash shot the last few streams onto her face, the size of the shots was still large causing Jessie's gorgeous features to be covered by a gooey mask.

 _"He came so much! I love the taste, tastes like vanilla pudding."_ She thought after swallowing the cum still in her mouth and throat before shivering. _"And he made me cum so hard just by sucking his dick. I can't wait to see how I'll reacted to having his cock inside me."_

 _"Holy shit! That was amazing! If this is what I've been missing out on, I would've had sex a long time ago."_ Ash thought getting his bearings back. He then looked at Jessie to see her covered in his cum and the sight made him hard again. _"Now that is a fucking sight to see."_

"So much cum." Jessie moaned using her fingers to clean her face of Ash's thick cum and licking them clean.

"That was awesome Jessie. You do this kind of thing before?" Ash asked.

"No, actually. You're my first in everything. My first kiss, my first blowjob..." Jessie said before smirking slithered her body over his as her pussy was resting on Ash's cock. "And now you'll be the first in taking my virginity."

"I'll make sure to treat you right." Ash promised.

Hearing that made Jessie have tears in her eyes before she kissed Ash lovingly as he kissed her back with equal passion.

"Thank you, Ash. That's just what I needed to hear." Jessie said before putting her left hand on his chest and lifted herself up using her right hand to grab hold of his dick and put his head on the lips of her pussy. "Ready to become a man?" She asked.

"Ready as you becoming a woman." Ash responded.

Not needing to wait anymore Jessie impaled herself down on Ash's pole spearing 7 inches into her breaking her hymen and taking her virginity. While Ash groaned at how tight her pussy was clamping down on him Jessie screamed with pleasure and just a little pain, she had never felt so stretched like this in her life. The toys she had pale in comparison to what she was feeling. Feeling a few more inches needed to go in Jessie ignored the pain and slammed the rest of Ash's cock inside her feeling the tip of him go into her womb making them both moaned more.

"Shit Jessie! You're so fucking tight!" Ash gritted.

"Arcues Ash! Y-You're huge!" Jessie groaned.

Seeing that Jessie was in discomfort a little Ash rubbed his hands on her tush before slowly rubbing the sides of her stomach then her breasts making Jessie sigh from actions he was doing to her body. They stayed like this for a few minutes with Ash rubbing Jessie's body to ease the pain.

"A-Ash, I'm ok now. You can move." Jessie said.

"If you're sure." Ash said.

Ash started fucking his cock into Jessie at a rapid tempo making her moan feeling his large cock sawing into her body. His hands rested her shapely hips as he was thrusting into her body causing her cunt to hug tightly on his tower like they were fleshy gums knawing on a toy.

"Jessie you feel so damn good!" Ash moaned in pleasure driving his cock deeper inside of her driving her crazy as more of it went inside of her womb making her shout shaking her head.

"Ash! You're a fucking god with this huge dick! I'm going crazy!" Jessie screamed in bliss resting her hands on his chest and twerked her hips harder on his twitching flesh.

The wet slapping of their sex reached their ears and added to their immense pleasure. Ash's right hand groped her bottom flesh while his left hand stayed on her hips rubbed up and down, pinching the tight flesh.

"Oh my fucking Arceus!" Breathed out Jessie bending her head down to curtain the two in her sweet-smelling hair. She closed her eyes to fully enjoy Ash's man-meat and try to memorize the girth and shape of it, even though she knew her pussy did that for her. "Come on Ash, touch my boobs." She pleaded seeing how he looked at them with lust, Ash took his left hand from her hips and brought it to her jiggling right orb. "It feels so fucking good. You make me feel wanted like a loving woman to her man." Jessie said with a cute blush adoring her lust warped face.

"Sorry, Jessie. It's just... you're so beautiful right now." Complemented Ash as his hand dug into her plentiful breast flesh with his other hand doing the same to her lower cheeks. "Your body... it's amazing!" Ash marveled at how soft and smooth her skin was and how she took his pounding. The rippling of her flesh was a treat to his eyes as her abused pussy was leaking their mixed juices. He could feel her walls constantly tightening around his manhood and knew she was enjoying them having sex.

"Thank you Ash! I can't get enough of this! It feels like my pussy is trying to make you stay inside of me." Jessie yelled as drool started coming out on the right side of her mouth fucking herself on his rampaging pole like a Rapidash in mating season.

"I can feel it! Your pussy is amazingly hot and tight!" Ash groaned, loving how her pussy was squeezing trying to suck more of him inside her. His balls ached a little as her tight walls got tighter. The slight pain actually increased his pleasure and showed it by slapping her bountiful ass and twerking her hard nipple. "You got even tighter!" He groaned in delight of her pussy walls clenching tighter around his thrusting cock.

"And, your cock is so hot and hard! I feel like I'm melting!" Jessie said, bringing herself closer to her lover. Their new position made Ash's hand release her bust but it was soon squashed against his chest, giving greater pleasure to both. Jessie's hips twerked up and down his cock even harder. Ash's free hand joined the other as both hands were now firmly squeezing her butt. "Kiss me!" She begged Ash, looking at him with love with her lips puckered.

He was more than happy to oblige to her plea. Their lips met in the middle in a passionate duel as they continued to lay with the other. Ash and Jessie groaned into one another's mouths. Both loved the others tastes. Using what knowledge she had, she squeezed her walls tighter around his rampaging prick while bucking herself up and down his shaft.

"This keeps getting better and better!" Ash groaned hard into the kiss as he used his hands to bring Jessie's delicious body back down whenever she slammed herself down. She screamed harder as the kiss got sloppier. Lips disconnecting, their tongue lashed out against the other in the air in a lewd dance. Saliva dripped down their mouths and to the couch that was stained with large wet spots from the sloshing cunt of Jessie's pussy.

As they continued to screw, Jessie was sure Ash could hear her heart beating like she could his through their connection. Her body was growing hotter and hotter with each slam. Her blue eyes snapped to life when she felt Ash's finger lightly brush against her rosebud. "AHHH! No!" Jessie's head was thrown back in the air as she moaned like a bitch in heat as Ash teased her bottom. She gulped in air that was continuously knocked from her by his powerful erection.

Biting his lip, Ash roared as he sat up and embraced Jessie, his head buried between her bountiful tits. "Jessie, I'm cumming!" He gritted his teeth.

"Cum inside me! I want to feel your hot cum inside my pussy!" Jessei wailed wrapping her arms around his head burying it deeper into her bosom.

"Here it comes!" Ash roared shooting out a large load of his semen inside of Jessie's body making her shout her shout her head off at the amazing feeling of cum flowing inside of her womb as Ash continued to groan into her bosom while still hammering himself in and out of her pussy still cumming. "I'm cumming deep inside your pussy, Jessie!"

"YESH~!" Jessie slurred as her tongue refused to stay between her supple lips feeling more of Ash's cum go inside of her. She stared in astonishment as her belly swelled even further as Ash pumped load after load deep into her. "You cumming so hard inside of me I look pregnant! It's such a turn on!" She wailed feeling her mind going numb.

When Ash's orgasm died and his cocked slipped out of Jessie's pussy the two were breathing hard and heavy trying to get the air back in their lungs.

"T-That was amazing. I had no idea sex could be so good." Jessie whimpered.

"I know what you mean. That was incredible." Ash huffed.

Once they got their breath back Ash and Jessie looked into each others eyes as deep blue and amber brown with blue tilt gazed at each other, feeling like they needed to they kissed passionately crawling their tongues around each other trying to show the other how much they appreciated them right now. They seperated and smiled at each other.

"Well Ash, you certainly know how to show a girl a good time." Jessie said.

"The same could be said for you, Jessie." Ash said.

Jessie made her way to get off of him but she felt his still hard dick as if he was ready for more.

"Seems like you want more of my body, you stud." Jessie teased.

"Well I got a sexy woman in my lap how can I not." Ash retorted.

"Well then I guess I'll just have to continue fucking you til those balls are dry."

"You're welcome to try."

With that Ash and Jessie kissed again and spent the whole night having sex with each other. Neither knowing that the sex life was just beginning.

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 **That's the first chapter of many. So stay tune for more.**


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